GB1396748A - 4-4-biphenylyl - butyramides - Google Patents
4-4-biphenylyl - butyramidesInfo
- Publication number
- GB1396748A GB1396748A GB3871272A GB3871272A GB1396748A GB 1396748 A GB1396748 A GB 1396748A GB 3871272 A GB3871272 A GB 3871272A GB 3871272 A GB3871272 A GB 3871272A GB 1396748 A GB1396748 A GB 1396748A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- biphenylyl
- reacting
- reducing
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/58—One oxygen atom, e.g. butenolide
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1396748 4 - (4 - Biphenylyl) - butyric acid amides DR KARL THOMAE GmbH 18 Aug 1972 [20 Aug 1971 (3)] 38712/72 Heading C2C The invention comprises 4-(4-biphenylyl)- butyric acid amides of the Formula I wherein A is R 1 is halogen, H, NO 2 , NH 2 or CN with the proviso that where A is -CH 2 CH 2 CH 2 - R 1 is halogen; R 2 is H or halogen; and R 3 and R 4 each are H, C 1-5 alkyl optionally substituted by H or C 1 -alkoxy, or phenyl optionally substituted by halogen, OH, CF 3 , C 1 -alkyl or C 1 -alkoxy; or R 3 and R 4 together with the nitrogen atom to which they are attached form a 1-pyrrolidinyl, piperidino, morpholino or 1-piperazinyl group each of which may be substituted by C 1 -alkyl, and acid addition salts of these compounds which contain basic nitrogen atoms. The compounds are prepared by reacting compounds of the formula wherein A is -CHOH-CH 2 CH 2 -, X is OR, where R is alkyl, aryl or aralkyl, and A is -COCH 2 CH 2 - or -CH 2 CH 2 CH 2 -, X is O-CO-OR, O-CO-R or OR or halogen or OH with the proviso that X may not be OH unless A is CH 2 CH 2 CH 2 with compounds of the formula HNR 3 R 4 , and, if necessary, removing protecting groups from any protected amino groups present. Compounds in which A is -COCH 2 CH 2 - may also be prepared by reacting the corresponding 5-(4-biphenylyl)-2(3H)- furanones, obtained by treating the appropriate 4 - (4 - biphenylyl) - 4 - oxobutyric acids with acetic anhydride; with compounds of the formula HNR 3 R 4 , or by reducing the corresponding 4 - (4 - biphenylyl) - 4 - oxocrotonic acid amides. Compounds in which A is may also be made by reducing compounds in which A is .COCH 2 CH 2 , or by reducing a mixture of such compounds with the corresponding 1 - R 3 - 5 - (4 - biphenylyl) - 5 - hydroxy - 2- pyrrolidinones, or by reducing the corresponding 4-(4-biphenylyl)-4-oxocrotonic acid amides or 4- (4-biphenylyl)-4-hydroxy-crotonic acid amides, or by reacting the appropriate γ-(4-biphenylyl)- γ-butyrolactones with compounds of the formula NHR 3 R 4 . Compounds in which A is may also be obtained by reducing compounds in which A is -COCH 2 CH 2 or Compounds in which R 1 is NH 2 may be prepared by reducing the corresponding compounds of Formula I in which R 1 is NO 2 . 4 - (2<SP>1</SP>,3<SP>1</SP> - Dichloro - 4 - biphenylyl) - butyric acid chloride is obtained by reacting the acid with thionyl chloride. 4 - (2<SP>1</SP> - Fluoro - 4 - biphenylyl) - 4 - oxo - N- propylcrotonamide is obtained by the mixed anhydride of the acid with ethyl chloroformate with propylamine. 4 - (2<SP>1</SP> - Nitro - 4 - biphenylyl) - 4 - oxobutyric acid benzoic anhydride is made by reacting the acid with benzoyl chloride. 5 - (2<SP>1</SP> - Fluoro - 4 - biphenylyl) - 1 - ethyl - 5- hydroxy-2-pyrrolidinone is obtained by reacting γ - (4<SP>1</SP> - fluoro - 4 - biphenylyl)-γ-butyrolactone with ethylamine. Pharmaceutical compositions, suitable for oral, parenteral or rectal administration, contain the above novel compounds or pharmaceutically acid addition salts of those compounds having basic nitrogen atoms in association with pharmaceutical carriers or diluents. The compounds possess antiphlogistic activity.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2141926A DE2141926A1 (en) | 1971-08-20 | 1971-08-20 | 4-(4-biphenylyl)-4-hydroxybutyramide derivs - with antiphlogistic activity |
DE2141925A DE2141925A1 (en) | 1971-08-20 | 1971-08-20 | 4-(4-biphenylyl)-4-oxobutyramides - with antiphlogistic activity |
DE2141927A DE2141927A1 (en) | 1971-08-20 | 1971-08-20 | 4-(4-biphenylyl)-butyramide derivs - with antiphlogistic activity |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1396748A true GB1396748A (en) | 1975-06-04 |
Family
ID=27183652
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3871272A Expired GB1396748A (en) | 1971-08-20 | 1972-08-18 | 4-4-biphenylyl - butyramides |
Country Status (6)
Country | Link |
---|---|
US (1) | US3882174A (en) |
BE (1) | BE787782A (en) |
FR (1) | FR2150809B1 (en) |
GB (1) | GB1396748A (en) |
IL (1) | IL40161A0 (en) |
NL (1) | NL7211363A (en) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ATA785173A (en) * | 1972-08-17 | 1975-01-15 | Thomae Gmbh Dr K | PROCESS FOR PREPARING NEW 4- (4-BIPHENYLYL) -4-HYDROXY-BUTTERIC ACID AMIDES |
US4060533A (en) * | 1976-06-25 | 1977-11-29 | Sandoz, Inc. | Pyranone carboxamides |
IL115995A0 (en) * | 1994-11-15 | 1996-01-31 | Bayer Ag | Substituted 4-biarylbutyric or 5-biarylpentanoic acids and derivatives as matrix metalloprotease inhibitors |
US5789434A (en) * | 1994-11-15 | 1998-08-04 | Bayer Corporation | Derivatives of substituted 4-biarylbutyric acid as matrix metalloprotease inhibitors |
MXPA03011558A (en) * | 2001-06-12 | 2004-03-26 | Wellstat Therapeutics Corp | Compounds for the treatment of metabolic disorders. |
CN105085433B (en) * | 2014-05-19 | 2019-06-25 | 中国科学院上海药物研究所 | Substituted amide phenol compound and preparation method thereof, pharmaceutical composition and purposes |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3624142A (en) * | 1964-09-10 | 1971-11-30 | Merck & Co Inc | Substituted biphenyl acetic acid derivatives |
-
0
- BE BE787782D patent/BE787782A/en unknown
-
1972
- 1972-08-18 FR FR7229733A patent/FR2150809B1/fr not_active Expired
- 1972-08-18 NL NL7211363A patent/NL7211363A/xx unknown
- 1972-08-18 IL IL40161A patent/IL40161A0/en unknown
- 1972-08-18 GB GB3871272A patent/GB1396748A/en not_active Expired
- 1972-08-21 US US282363A patent/US3882174A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
IL40161A0 (en) | 1972-10-29 |
US3882174A (en) | 1975-05-06 |
NL7211363A (en) | 1973-02-22 |
FR2150809B1 (en) | 1976-03-05 |
BE787782A (en) | 1973-02-19 |
FR2150809A1 (en) | 1973-04-13 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
ES477457A1 (en) | 4-Amino-6,7-dimethoxyquinazol-2-yl alkylenediamines | |
DE19575041I2 (en) | Substituted acyl derivatives of 1, 2, 3, 4-tetrahydro-6, 7-dimethoxy-3-isoquinoline carboxylic acid | |
MC1596A1 (en) | COMPOUNDS USEFUL FOR THE TREATMENT OF ALLERGIC CONDITIONS | |
GB1467471A (en) | Derivatives of 1,3-disubstituted-2,4-quinazolinediones | |
ES2171400T3 (en) | DERIVATIVES OF PHENYL-ACETIC ACID USED AS MEDICINES. | |
IE40511B1 (en) | N-(1-(-phenylalkyl)-piperidyl-j)-(-(-pyridyl)-carbonic acid amides | |
GB1396748A (en) | 4-4-biphenylyl - butyramides | |
GB1225462A (en) | ||
GB1431414A (en) | Prostanoic acid derivatives | |
GB1398638A (en) | Furan 2-or 3-carboxylic and amides compositions thereof and methods for using same | |
GB1292787A (en) | Benzodioxane derivatives and pharmaceutical compositions containing them | |
GB1458029A (en) | Sulphamylbenzoic acids and preparation thereof | |
GB1111361A (en) | 4-phenoxyalkanoic acids and derivatives thereof | |
GB1299201A (en) | Medicaments derived from thiazolidine carboxylic acid | |
GB1444492A (en) | Butyramides their preparation and pharmaceutical compositions containing them | |
GB1314952A (en) | 3,4,5-trialkoxy-benzoic acid derivatives and their uses | |
GB1464431A (en) | Indolobenzazepine derivatives and a process for the manufacture thereof | |
US3974192A (en) | 16-Fluoro prostaglandin B1 analogs | |
GB1135907A (en) | Process for the production of coumarin derivatives | |
US3974190A (en) | 16-Fluoro prostaglandin A1 analogs | |
GB1242096A (en) | Benzobenzofuranooxepine compounds and process for preparing the same | |
GB1462676A (en) | Substituted esters of n-4-quinolyl-anthranilic acids | |
GB1392270A (en) | Indan-1-carboxamide derivatives | |
GB1029213A (en) | Chromone derivatives | |
DE2964141D1 (en) | Alpha-ethinyl-alpha-aminoacids and their esters, and pharmaceutical compositions containing them |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
CSNS | Application of which complete specification have been accepted and published, but patent is not sealed |